EP0795543B1 - Utilisation de solvants ou de mélanges de solvants à point d'ébullition élevé comme fluide d'échange de chaleur dans la décomposition thermique d'esters carbamiques - Google Patents
Utilisation de solvants ou de mélanges de solvants à point d'ébullition élevé comme fluide d'échange de chaleur dans la décomposition thermique d'esters carbamiques Download PDFInfo
- Publication number
- EP0795543B1 EP0795543B1 EP97103444A EP97103444A EP0795543B1 EP 0795543 B1 EP0795543 B1 EP 0795543B1 EP 97103444 A EP97103444 A EP 97103444A EP 97103444 A EP97103444 A EP 97103444A EP 0795543 B1 EP0795543 B1 EP 0795543B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- bis
- column
- methoxycarbonylamino
- boiling
- carbamic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/04—Preparation of derivatives of isocyanic acid from or via carbamates or carbamoyl halides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Definitions
- the invention relates to the use of defined or in a narrow range boiling inert thermostable solvents or mixtures as a heat exchange medium for the thermal cleavage of carbamic acid esters (urethane cleavage).
- the splitting in the liquid phase enables compared to the gas phase splitting low reaction temperatures of ⁇ 300 ° C, but requires quick separation of the reaction products.
- this causes the back reaction of isocyanate and hydroxyl component to avoid the carbamic acid ester
- the formation of resinous by-products that lead to deposits in the apparatus can, reduced or avoided.
- an inert solvent By dilution with an inert solvent the formation of higher molecular weight secondary products can be reduced, at the same time, the solvent is used to discharge these secondary components.
- the Reaction takes place in the evaporator area, the solvent being evaporated and condensation transports the thermal energy from the evaporator to the reaction zone.
- the cleavage of the carbamic acid ester can be carried out in such a cleavage and rectification column be operated so that no carbamic acid ester with the heating surfaces comes into contact in the evaporator and thus long operating times of the Apparatus are possible.
- a cleavage and rectification column be operated so that no carbamic acid ester with the heating surfaces comes into contact in the evaporator and thus long operating times of the Apparatus are possible.
- the reactor described in EP-A 0 524 554 is only a small discharge of the swamp contents is necessary, because at this point neither carbamic acid esters nor cleavage or by-products can be detected analytically are.
- the carbamic acid esters to be used in the process according to the invention are compounds of the general formula R 1 (NHCOOR 2 ) n .
- the high boilers which can be used according to the invention include, for example, the compounds mentioned in US Pat. di (ar) alkyl esters, o-phosphoric acid tri (ar) alkyl esters each having 1 to 10 carbon atoms in the (ar) alkyl esters or any mixtures of such compounds.
- Technical dibenzyltoluene, benzyl n-butyl phthalate, technical terphenyl or partially hydrogenated terphenyls, phenoxybiphenyls or their isomer mixtures are particularly suitable for use in the cleaving and rectifying columns mentioned.
- the object of the invention was therefore to provide suitable solvents or solvent mixtures combined for the thermal cleavage described in more detail below To provide cleavage and rectification columns.
- a suitable, high-boiling solvent prevents the reaction in the Evaporator area expires, the solvent through evaporation and condensation the thermal energy is transported from the evaporator into the reaction zone and thus acts as a heat exchange medium.
- the invention relates to the use of a solvent which defined boiling point (pure substance) or a narrow boiling range ⁇ 10 ° C, preferably ⁇ 6 ° C, particularly preferably ⁇ 3 ° C at operating pressure, and which is obtained as a distillation cut from thermostable liquids, selected from the group of ortho, meta and para isomers of phenoxybiphenyl for the thermal cleavage of carbamic acid esters.
- a solvent which defined boiling point (pure substance) or a narrow boiling range ⁇ 10 ° C, preferably ⁇ 6 ° C, particularly preferably ⁇ 3 ° C at operating pressure, and which is obtained as a distillation cut from thermostable liquids, selected from the group of ortho, meta and para isomers of phenoxybiphenyl for the thermal cleavage of carbamic acid esters.
- the amplifier and middle part of the Column at compared to the reaction part depending on the bottom pressure operated up to 900 mbar reduced pressure, the separation of the Pressure levels, if necessary, by separating the amplifier and middle part of the Column can be done in a separate apparatus.
- the back reaction can also be done by only in the amplifier section reduced pressure can be counteracted, resulting in a reduced temperature and thus leads to a slowed back reaction.
- Rectification columns are suitable as apparatus which have a stripping section with sufficient have a high dwell time and an amplifier part with a low dwell time.
- the dwell time in the stripping section is based on the gap and mass transfer kinetics vote and is therefore strongly dependent on the material system, it is 1 to 1000 min, preferably 5 to 200 min and is here as the quotient of liquid hold-up defined in the stripping section and inlet volume flow of the liquid phase.
- Low-pressure packs with high hold-up are combined with a preference is given to narrow-boiling solvents, since this means that a approximately constant over the reaction part of the column and over the absolute pressure freely selectable temperature succeeds.
- the temperature in the reaction zone should preferably be selected in a temperature range in which the Reaction proceeds sufficiently quickly and on the other hand the formation of not recyclable by-products not yet used or only very weakly.
- the column has a return at the top of the column, at least one side draw for the partial or complete removal of the liquid phase as well as a sump drain.
- the fission products can also be separated by dephlegmators, preferably they are separated by rectification.
- the reactor feed consists of the carbamic acid ester, optionally one Catalyst and / or the inert solvent used according to the invention and if applicable, from the by-products that arise in a closed-loop process, in which from an amine, a carbonyl source such as oxides of Carbon or carbonic acid derivatives, preferably urea and / or carbamic acid esters or dialkyl carbonates and a hydroxyl component a carbamic acid ester will be produced.
- the recycled solvent can optionally partially or completely introduced directly into the bottom of the column.
- the feed stream of the column is generally composed of the Main stream from the preceding process step and optionally a) the low-by-product partial stream that results from the bottom discharge of the column after removal of higher boiling by-products results and optionally b) from the bottom discharge of the pure column and optionally c) Fresh solvent and optionally d) top product of the pure column.
- the Inlet is preheated to a temperature which is up to 250 ° C above Melting temperature of the carbamic acid ester, preferably 50 ° C below that Reaction temperature is.
- the inlet is above the stripping section in the Column fed.
- catalysts e.g. Metals, metal oxides, inorganic or organic Metal compounds and acidic additives.
- the column is operated at a bottom pressure of 2 to 1000 mbar, the pressure range from 20 to 200 mbar is preferred.
- the bottom temperature is 150 to 400 ° C, preferably 220 to 300 ° C. It is essentially directed according to the boiling point of the solvent and should also be chosen so that side reactions of the carbamic acid ester occur only weakly.
- the reflux ratio the head is between 0.2 and 20, preferably 2 to 10.
- the reflux ratio the sidestream draw is between 0 and 40, preferably between 5 and 20.
- the sump discharge serves to discharge by-products and the Removal of high-boiling contaminants, which if necessary (e.g. together with the carbamic acid ester).
- the sump discharge serves to discharge by-products and the Removal of high-boiling contaminants, which if necessary (e.g. together with the carbamic acid ester).
- the Amount of solvent to be added or removed as to maintain a predetermined By-product concentration in the sump is necessary.
- EP-A 0 524 554 and DE-A 42 31 417 are complete Cleavage of the carbamic acid ester usually already during the first column run, so that normally no educt has to be circulated.
- a downstream apparatus can remove high-boiling contaminants from the Bottom withdrawal stream in a manner known per se, e.g.
- the bottom of the fine distillation is usually the inlet of the column admixed with a larger proportion of higher molecular reaction by-products the swamp can also be wholly or partly in the stage of urethane production be returned or removed.
- HDU-B hexamethylene di-n-butyl urethane-1,6
- the column consists of an evaporator with 4 horizontally arranged heating plugs. Above this, in the stripping section, there is an orderly pack with a diameter of 70 mm and a liquid hold-up of around 1500 ml over a length of 8.1 m. Above this reaction zone is the inlet, with the HDU-B with 120 ° C and the solvent is metered in at 160 ° C. The middle part of the column has a diameter of 70 mm and is filled with tissue packs over an effective height of 990 mm. This is followed by the side stream extraction and 850 mm effective tissue pack with 50 mm diameter. The top of the column consists of the liquid divider and a water-cooled condenser. The column is isolated.
- the top reflux ratio was 7 in the example, the side stream reflux ratio 10.
- the top pressure in this example was 85 mbar and the bottom temperature was 260 ° C.
- 0.3 kg / h of liquid were withdrawn from the column bottom and, according to Supercritcal Fluid Chromatography (SFC), contained only the heat transfer medium, HDU-B or its secondary products were not detectable (detection limit 0.1%).
- SFC Supercritcal Fluid Chromatography
- the same finding was obtained by IR analysis.
- the liquid that dripped from the distillation column into the sump and was removed from the sample was just as pure; here, too, no impurities were found using SFC or IR analysis.
- the side stream of 0.48 kg / h consisted of 98.2% by weight HDI, 1.6% by weight semi-split product of the formula (I) BuOCONH- (CH 2 ) 6 -NCO
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (3)
- Utilisation d'un solvant à point d'ébullition défini (substance pure) ou à intervalle d'ébullition étroit, inférieur à 10°C à la pression opératoire, obtenu en coupe de distillation de liquides stables à la chaleur, et choisi dans le groupe des isomères ortho, méta et para du phénoxybiphényle, pour la scission des esters carbamiques à la chaleur.
- Utilisation selon la revendication 1, caractérisée en ce que l'on utilise en tant que produits à haut point d'ébullition des coupes de distillation du phénoxybiphényle et de l'o-phénoxybiphényle du commerce, agents d'échange de chaleur à un intervalle d'ébullition inférieur à 3°C (à la pression opératoire).
- Utilisation selon la revendication 1, caractérisée en ce que la scission est réalisée dans une colonne de rectification réactive.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19610261 | 1996-03-15 | ||
DE19610261 | 1996-03-15 | ||
DE19618828A DE19618828A1 (de) | 1996-05-10 | 1996-05-10 | Verwendung von hochsiedenden Lösemitteln bzw. -gemischen als Wärmetauschmedium für die thermische Spaltung von Carbamidsäureestern |
DE19618828 | 1996-05-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0795543A1 EP0795543A1 (fr) | 1997-09-17 |
EP0795543B1 true EP0795543B1 (fr) | 2001-10-31 |
Family
ID=26023837
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97103444A Expired - Lifetime EP0795543B1 (fr) | 1996-03-15 | 1997-03-03 | Utilisation de solvants ou de mélanges de solvants à point d'ébullition élevé comme fluide d'échange de chaleur dans la décomposition thermique d'esters carbamiques |
EP97103445A Expired - Lifetime EP0795544B1 (fr) | 1996-03-15 | 1997-03-03 | Procédé de décomposition thermique d'esters carbamiques |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97103445A Expired - Lifetime EP0795544B1 (fr) | 1996-03-15 | 1997-03-03 | Procédé de décomposition thermique d'esters carbamiques |
Country Status (6)
Country | Link |
---|---|
US (2) | US5883291A (fr) |
EP (2) | EP0795543B1 (fr) |
JP (2) | JP4031551B2 (fr) |
CA (2) | CA2199919A1 (fr) |
DE (2) | DE59705128D1 (fr) |
ES (2) | ES2166923T3 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011067242A1 (fr) | 2009-12-01 | 2011-06-09 | Basf Se | Procédé de fabrication d'isocyanates par dissociation thermique de carbamates |
WO2011067369A1 (fr) | 2009-12-04 | 2011-06-09 | Basf Se | Procédé de production d'isocyanates |
WO2011089098A1 (fr) | 2010-01-19 | 2011-07-28 | Basf Se | Procédé de production d'isocyanates par craquage thermique de carbamates |
WO2016156188A1 (fr) | 2015-03-31 | 2016-10-06 | Basf Se | Procédé de production d'isocyanates par craquage de carbamate |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6008396A (en) * | 1997-04-11 | 1999-12-28 | Osi Specialties, Inc. | Hot oil process for producing isocyanato organosilanes |
AU7469598A (en) * | 1997-05-09 | 1998-11-27 | Dow Chemical Company, The | Thermal fluid blends containing 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene |
US6350927B2 (en) | 1997-05-09 | 2002-02-26 | The Dow Chemical Company | Thermal fluid blends containing 1,2,3,4-tetrahydro (1-phenylethyl)naphthalene |
DE19813107A1 (de) | 1998-03-25 | 1999-09-30 | Basf Ag | Verfahren zur Herstellung von Polyurethanschaumstoffen |
CN1186317C (zh) | 2000-02-29 | 2005-01-26 | 亨茨曼国际有限公司 | 制备有机多异氰酸酯的方法 |
SG115512A1 (en) | 2001-12-28 | 2005-10-28 | Mitsui Takeda Chemicals Inc | Method for producing carbamates and method for producing isocyanates |
US8053595B2 (en) * | 2006-11-17 | 2011-11-08 | Asahi Kasei Chemicals Corporation | Process for producing isocyanates |
TW200844080A (en) * | 2007-01-11 | 2008-11-16 | Asahi Kasei Chemicals Corp | Process for producing isocyanate |
CA2682512C (fr) | 2007-03-30 | 2012-03-06 | Asahi Kasei Chemicals Corporation | Procede de production d'isocyanate utilisant une composition comprenant un ester d'acide carbamique et un compose hydroxy aromatique, et une composition pour le transport ou le stockage d'ester d'acide carbamique |
RU2523201C2 (ru) * | 2008-05-15 | 2014-07-20 | Асахи Касеи Кемикалз Корпорейшн | Способ получения изоцианатов с использованием диарилкарбоната |
CA2721359C (fr) * | 2008-05-15 | 2014-05-06 | Asahi Kasei Chemicals Corporation | Procede de production d'isocyanate |
US8680323B2 (en) | 2010-01-19 | 2014-03-25 | Basf Se | Process for preparing isocyanates by thermal dissociation of carbamates |
WO2011161029A1 (fr) | 2010-06-22 | 2011-12-29 | Basf Se | Dissociation de carbamate en présence d'un catalyse hétérogène pour la synthèse d'isocyanates sur des acides de lewis solides |
CN103140473B (zh) | 2010-10-04 | 2016-06-01 | 旭化成株式会社 | 分离方法和异氰酸酯的制造方法 |
CN102653517A (zh) * | 2011-03-02 | 2012-09-05 | 中国科学院过程工程研究所 | 一种由氨基甲酸酯制备异氰酸酯的方法 |
CA2857821C (fr) | 2012-01-25 | 2015-09-08 | Asahi Kasei Chemicals Corporation | Methode de separation |
JP5650777B2 (ja) * | 2013-03-11 | 2015-01-07 | 旭化成ケミカルズ株式会社 | 炭酸ジアリールを用いるイソシアネートの製造方法 |
US9663539B2 (en) | 2014-07-14 | 2017-05-30 | Momentive Performance Materials Inc. | Process for producing low-color and color-stable isocyanatoorganosilanes and products derived therefrom |
JP6757468B2 (ja) | 2017-05-15 | 2020-09-16 | 旭化成株式会社 | イソシアネートの製造方法 |
JP2021531267A (ja) * | 2018-07-13 | 2021-11-18 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッドMomentive Performance Materials Inc. | イソシアナトシランの調製 |
CN111303373B (zh) * | 2020-02-25 | 2022-07-12 | 万华化学集团股份有限公司 | 一种低色度脲基甲酸酯组合物及其制备方法和应用 |
CN116177484A (zh) * | 2023-03-04 | 2023-05-30 | 福州大学 | 一种液体有机氢载体全氢苄基甲苯的反应精馏脱氢工艺 |
Citations (2)
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US3919278A (en) * | 1974-06-13 | 1975-11-11 | Atlantic Richfield Co | Production of isocyanates from lower alkyl esters of mononuclear aromatic carbamic acids |
DE4231417A1 (de) * | 1992-05-05 | 1993-11-11 | Huels Chemische Werke Ag | Kontinuierliches mehrstufiges Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
Family Cites Families (21)
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US3734941A (en) * | 1968-09-06 | 1973-05-22 | American Cyanamid Co | Process for converting urethanes to isocyanates |
US3870739A (en) * | 1973-03-05 | 1975-03-11 | Air Prod & Chem | Isocyanates from urethanes |
DE2942543A1 (de) * | 1979-10-20 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von arylisocyanaten durch thermische spaltung von arylurethanen |
DE3047898A1 (de) * | 1980-12-19 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern und die verwendung von hierbei anfallenden isocyanate und carbamidsaeureester aufweisenden gemischen zur herstellung von isocyanaten |
DE3108990A1 (de) * | 1981-03-10 | 1982-09-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyisocyanaten |
DE3142627A1 (de) * | 1981-10-28 | 1983-05-05 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von isocyanaten durch thermische spaltung von urethanen |
DE3215591A1 (de) * | 1982-04-27 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern |
EP0100047B1 (fr) * | 1982-07-24 | 1986-02-12 | BASF Aktiengesellschaft | Procédé de préparation du diisocyanate-1,6 d'hexaméthylène et/ou de diisocyanates isomères avec 6 atomes de carbone dans le groupe alkylène |
DE3314790A1 (de) * | 1983-04-23 | 1984-10-25 | Basf Ag, 6700 Ludwigshafen | Mehrstufenverfahren zur herstellung von 3-isocyanatomethyl-3,5,5-trimethyl-cyclohexylisocyanat |
DE3314788A1 (de) * | 1983-04-23 | 1984-10-25 | Basf Ag, 6700 Ludwigshafen | Mehrstufenverfahren zur herstellung von hexamethylendiisocyanat-1,6 und/oder isomeren aliphatischen diisocyanaten mit 6 kohlenstoffatomen im alkylenrest |
US4599401A (en) * | 1983-10-27 | 1986-07-08 | Union Carbide Corporation | Low viscosity adducts of poly(active hydrogen) organic compounds and a polyepoxide |
DE3339300A1 (de) * | 1983-10-29 | 1985-05-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von isocyanaten durch thermische spaltung von urethanen |
DE3632010A1 (de) * | 1986-09-20 | 1988-04-07 | Basf Ag | Neue 2-(alkoxymethyl)-pentan-1,5-diisocyanate, -diurethane und -dicarbamidsaeurechloride, verfahren zu ihrer herstellung und deren verwendung |
DE3850647T2 (de) * | 1987-01-13 | 1994-11-17 | Daicel Chem | Verfahren zur herstellung von isocyanat-verbindungen. |
DE3828033A1 (de) * | 1988-08-18 | 1990-03-08 | Huels Chemische Werke Ag | Kreislaufverfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
DE3915181A1 (de) * | 1989-05-10 | 1990-11-15 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten |
DE4010226A1 (de) * | 1990-03-30 | 1991-10-02 | Basf Ag | Neue 2,2-dialkylpentan-1,5-diisocyanate, -diurethane und -dicarbamidsaeurechloride, verfahren zu ihrer herstellung und ihre verwendung |
DE4124671A1 (de) * | 1991-07-25 | 1993-01-28 | Basf Ag | Reaktor und verfahren zur thermischen spaltung von carbamidsaeureestern |
DE4137428A1 (de) * | 1991-11-14 | 1993-05-19 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten |
DE4213099A1 (de) * | 1992-04-21 | 1993-10-28 | Basf Ag | Mehrstufiges Verfahren zur kontinuierlichen Herstellung von organischen Polyisocyanaten |
DE4413580A1 (de) * | 1994-04-19 | 1995-10-26 | Bayer Ag | Verfahren zur Herstellung von 1,4-Diisocyanatobutan (BDI) |
-
1997
- 1997-03-03 DE DE59705128T patent/DE59705128D1/de not_active Expired - Lifetime
- 1997-03-03 ES ES97103445T patent/ES2166923T3/es not_active Expired - Lifetime
- 1997-03-03 EP EP97103444A patent/EP0795543B1/fr not_active Expired - Lifetime
- 1997-03-03 DE DE59705127T patent/DE59705127D1/de not_active Expired - Lifetime
- 1997-03-03 EP EP97103445A patent/EP0795544B1/fr not_active Expired - Lifetime
- 1997-03-03 ES ES97103444T patent/ES2166922T3/es not_active Expired - Lifetime
- 1997-03-06 US US08/812,610 patent/US5883291A/en not_active Expired - Lifetime
- 1997-03-06 US US08/811,801 patent/US5731458A/en not_active Expired - Lifetime
- 1997-03-13 CA CA002199919A patent/CA2199919A1/fr not_active Abandoned
- 1997-03-13 JP JP07671597A patent/JP4031551B2/ja not_active Expired - Fee Related
- 1997-03-13 CA CA002199913A patent/CA2199913C/fr not_active Expired - Fee Related
- 1997-03-13 JP JP07671497A patent/JP4031550B2/ja not_active Expired - Fee Related
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US3919278A (en) * | 1974-06-13 | 1975-11-11 | Atlantic Richfield Co | Production of isocyanates from lower alkyl esters of mononuclear aromatic carbamic acids |
DE4231417A1 (de) * | 1992-05-05 | 1993-11-11 | Huels Chemische Werke Ag | Kontinuierliches mehrstufiges Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
Non-Patent Citations (2)
Title |
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Beilstein database, Daten zur Verbindung Benzyl-n-butyl-phthalat * |
Kirk- Othmer, Encyclopedia Chem. Technol. 4th ed., vol. 4, Seite 225 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011067242A1 (fr) | 2009-12-01 | 2011-06-09 | Basf Se | Procédé de fabrication d'isocyanates par dissociation thermique de carbamates |
WO2011067369A1 (fr) | 2009-12-04 | 2011-06-09 | Basf Se | Procédé de production d'isocyanates |
WO2011089098A1 (fr) | 2010-01-19 | 2011-07-28 | Basf Se | Procédé de production d'isocyanates par craquage thermique de carbamates |
WO2016156188A1 (fr) | 2015-03-31 | 2016-10-06 | Basf Se | Procédé de production d'isocyanates par craquage de carbamate |
Also Published As
Publication number | Publication date |
---|---|
CA2199913A1 (fr) | 1997-09-15 |
EP0795544A1 (fr) | 1997-09-17 |
DE59705128D1 (de) | 2001-12-06 |
JPH09249633A (ja) | 1997-09-22 |
EP0795544B1 (fr) | 2001-10-31 |
ES2166923T3 (es) | 2002-05-01 |
JP4031551B2 (ja) | 2008-01-09 |
CA2199913C (fr) | 2006-05-16 |
EP0795543A1 (fr) | 1997-09-17 |
JPH09249632A (ja) | 1997-09-22 |
US5883291A (en) | 1999-03-16 |
CA2199919A1 (fr) | 1997-09-15 |
US5731458A (en) | 1998-03-24 |
ES2166922T3 (es) | 2002-05-01 |
DE59705127D1 (de) | 2001-12-06 |
JP4031550B2 (ja) | 2008-01-09 |
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